Instead of Florida, Why Not Consider a Long Stay in the Caribbean?

by | Aug 16, 2020

Caribbean Mature woman in bikini and sun hat sits on a beach
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Last updated on April 5th, 2024

Featured Image: In the midst of summer sun, it feels silly to consider the cold of winter, but now is the time, before blizzards ground flights, to plan your long-term, cold-weather getaways. / Photo credit: Matthias Stalt on Adobe Stock

10 countries to consider for longer stays in the Caribbean

by Nancy Drolet, Jesson & Co, and JourneyWoman Advisory Council member

Soon, snow and sub-zero temperatures will be upon us. While many Canadians visit Florida, why not consider the Caribbean this year?  Islands in the sun.  White-sand beaches, azure waters, swaying palm trees where warm trade winds blow.  Could the Caribbean be an alternative to wintering in Florida or Arizona this year?

(Please note: this article was written during the pandemic and some information may be outdated). 


View of downtown Toronto streets in a snowstorm from a streetcar window
It’s easy to forget about the snow and ice once summer hits, but come winter, slushy streets and freezing-cold treks are the norm. / Photo by Andre Furtado on Unsplash

Why the Caribbean could be a good choice

If you are thinking of going to the Caribbean this winter, here are some things to consider:

  • Accessibility: Canadian and American carriers are already flying to many Caribbean countries, including Antigua & Barbuda, St. Martin, the Bahamas and more. Flights are being added and although not up to pre-Covid levels, the signs are promising for more flights in the Fall and Winter seasons. With protocols in place to ensure safe travels, airlines are stepping up to the plate to ensure a clean and safe flight experience.
  • Food! With good food to be found all over the Caribbean, you’ll be hard pressed to choose from the array of restaurants. Most Caribbean countries offer a wide variety of foods from all over the world. Usually locally sourced food ensures fresh fruits and vegetables are available year-round. Grocery stores are accessible and food and spice markets are fun to explore.
  • Internet: Need to get some work done while you are away? Most Caribbean countries offer reliable service so you can take those zoom calls with minimal disruption.
  • Activities: You can live an active life in the Caribbean from walking, biking, hiking, swimming to diving, snorkelling, sailing etc. Truly relax by visiting world class spas or joining a yoga or meditation class. There are watersports galore to choose from. Interested in art or history? There are galleries and museums to visit. Rent a car to explore the island you are on. Want to visit another island while staying on one? There are ferries, sailboats and flights to allow you to hop to another island for a day or longer.
  • Accommodation: Variety is key here, from villas to apartments to condos to Airbnbs…there is a lot to choose from in terms of where to stay. There are also a range of price points to choose from. Have you considered sailing around the Caribbean for a few months? Companies such as The Moorings and Sunsail lease sailboats and yachts.
  • Health Care: Always a concern when travelling outside of your home country especially for seniors and retirees. Most Caribbean countries have top notch medical care, through on call doctors, clinics, pharmacies and hospitals.

Ten Countries to Consider for Long Stays

Over the years, I’ve been fortunate to work with Canadian tour operators, hotel chains and cruise lines with Caribbean products which gave me the opportunity to visit a number of Caribbean countries. I worked with the Sandals hotel chain as well as for Radisson Bahamas, and most recently promoted the Caribbean through my position with the Caribbean Tourism Organization where I worked with 24 member countries of the CTO.

Here’s my take on what’s happening.

Disclaimer: I work with companies marked with an (*).


Officially, Anguilla’s borders are closed until October 31. They have said that travellers from countries with less than 0.2% active cases of Covid-19 fill out an application to enter Anguilla; all visitors approved to arrive in Anguilla will be required to provide a negative PCR test taken within 3 to 5 days of arrival along with proof of insurance covering Covid related illnesses. We’re waiting on further details of potential opening dates and their protocols. Anguilla was recognized by the WHO for being Covid-19 free. They only ever had three cases – all recovered.


Sandy Island, Anguilla

Sandy Island, Anguilla / Photo provided by Nancy Drolet

Antigua & Barbuda*

Their borders opened on July 1 with their first flight from the US on July 4.. A few little hiccups, but their entry protocols have been working. They require a negative PCR test taken within 7 days of their arrival flight. Weekly flights from Toronto are scheduled to begin in September.


English Harbour, Antigua and Barbuda

English Harbour in Antigua & Barbuda / Photo credit: Ted Martin


Barbados is promoting “working remotely” for 12 months, an appealing idea! The airport opened to international travel on July 12 and has implemented strict travel protocols depending on which country you’re arriving from. You can view these here.


Beaches in Barbados
The simple, beautiful beaches of Barbados are calling / Photo by Anthony Ingham on Unsplash

The Bahamas*

The Bahamas reopened to tourists, then closed to Americans, then reopened to all BUT have implemented a 14-day quarantine on arrival. They require a negative PCR test taken within 10 days of their arrival flight. With 700 islands to consider, it’s an ideal destination for those who love yachting. Currently, Bahamians are in a lockdown situation (except for a few of the southern-most islands in the archipelago) as they had a resurgence of Covid-19. This lockdown is supposed to end in mid- August, but I do think it will be extended. There is a weekly flight from Canada, which will go to two flights weekly in September.


Junkanoo celebration in Bahamas

Celebrate like the locals do at Junkanoo in the Bahamas / Photo provided by Nancy Drolet


Flights from Canada will start in September to a few remote areas in Cuba like Cayo Coco. They will restrict travel to mainland Cuba, while welcoming travellers to the cays. This will allow visitors to travel within the cays…and keep the Cuban population away from the tourists.


Cayo Cruz, Cuba

Cayo Coco and other cays are relatively isolated from larger cities (Photo: C. Ray)  

St. Martin, French side*

The Dutch side is where the international airport is located and they have opened up to visitors. Although travel is normally open between the two sides, because of the Dutch side opening up to American visitors, the border between the two countries is currently closed – and will stay closed until at least September 1st. St. Martin is a French territory and must abide by the laws of France (currently US visitors are not allowed). Right now, we don’t have any scheduled flights to Saint Martin – and are awaiting updates from the airlines and tour operators.

Website for French side:

Baie de Marigot, French St Martin

English Harbour in Antigua & Barbuda / Photo credit: Ted Martin


Jamaica’s protocols have been changing for US visitors. All Americans are now required to upload a negative Covid-19 PCR test taken within 10 days of departure. Canadians are not considered high risk, and do not have to have a PCR test done in advance though they can be tested on arrival.  All travellers must stay in a zone – i.e. they do not have the run of the country!


Horse stands in the surf on the beach in Jamaica
Horseback-riding on the beach in Jamaica? Yes, please. / Photo by Austin Kirk on Unsplash


They have just opened up with a flight from Canada this week. Not all hotels are open. They will require a Rapid Test on arrival from low risk countries such as Canada, but other countries considered medium or high risk will require PCR test in advance.


Aerial view of Grenada
The rainbow colours of the island of Grenada / Photo by Hugh Whyte on Unsplash


Aruba recently changed their protocols for Americans as they had a resurgence of cases. Canadians must upload a PCR test prior to travelling to Aruba or at the airport upon arrival. There are direct flights to Aruba from Toronto (it’s a five-hour flight).


Santa Cruz, Aruba
So much to explore on the island of Aruba / Photo by Qijin Xu on Unsplash


Dominica, the ‘nature island’ offer a safe, varied environment with a place to enjoy beautiful scenery, beaches and self-care. The island requires a 14-day mandatory quarantine and is promoting long stays. To access Dominica, you must fly through Puerto Rico or another Caribbean island, such as Antigua, Barbados or St. Maarten.


Secret Bay Resort from above

Dominica – a modern-day Garden of Eden / Photo credit: Secret Bay Resort

Nancy Drolet is a 30-year veteran of the travel industry and a director at Jesson & Company, which represents several international destinations. Prior to that, she was the Caribbean Tourism Organization’s Canadian representative and has worked with travel companies, cruise lines, tour operators and hotels and resort across the Caribbean. You can read her full bio here.

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  1. Liz Franklin

    The problem with any country asking for travel/medical insurance that covers Covid is that is impossible. None of the insurance companies will cover this. I think travel will be back to some kind of normal for 2022 but not before. Too risky.

    • Rita

      Trawick is great traveler’s insurance that I have used twice (fall 2021 & Jan 2022), but there are many companies that specialize in this. Go to the website of the island you like; you will either ge required insurance offered through the government or lists of possible providers. Then, enjoy the sun.

  2. rosemary

    Seniors on the go, usually by bus through Peru, Vietnam, South Africa, so we now are contemplating hunkering down and being grateful to
    be in the sun. As I understand here, a stay would be localized, so no travelling within a country let alone island hop through the Caribbean, is that correct ? To island hop would mean a 2-week quarantine at each island, which is ok as that is what a hotel stay is, right? And presumably, this safety regimen will be part of travel to anywhere… pick a great spot and stay there!!


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